2,3,5-Trichlorobenzonitrile synthesis
- Product Name:2,3,5-Trichlorobenzonitrile
- CAS Number:6575-02-6
- Molecular formula:C7H2Cl3N
- Molecular Weight:206.46
36764-94-0
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Yield:6575-02-6 88%
Reaction Conditions:
with tert.-butylnitrite;copper dichloride in acetonitrile at 0 - 25; for 16 h;
Steps:
A.5.1 Example 5: Preparation of 5,7-dichloro-N-[1-(2-pyrimidin-2-yl-1,2,4-triazol-3-yl)ethyl]-1,2-ben- zothiazol-3-amine [I-5]:
Step 1: To a solution of 2-amino-3,5-dichloro-benzonitrile (200 mg, 1.07mmol) in MeCN (7ml_) at 0°C was added a solution of tert-butylnitrite (220 mg, 2.14mmol) and CuCl2 (172 mg, 2.14mmol) in MeCN (2mL). The resulting reaction mixture was allowed to warm to 25°C and stirred at that temperature for 16h. Then TLC (PE/EtOAc = 5:1, Rf = 0.5) showed the reaction was completed. The reaction mixture was quenched with H2O (20ml_), the aqueous phase was extracted with EtOAc (2x20 ml_), and the combined organic extracts were washed with NaCI solution (20ml_, sat. aq.), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by preparative TLC afforded 2,3,5-trichlorobenzonitrile (176 mg, 88 %) as a white solid. 1H-NMR (CDCI3, 400 MHz, RT): d ppm 7.72 (d, J=2.4Hz, 1H), 7.60 (d, J=2.4Hz, 1H).
References:
WO2021/228594,2021,A1 Location in patent:Page/Page column 29; 34
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56961-75-2
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